CA2144967C - Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents - Google Patents
Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents Download PDFInfo
- Publication number
- CA2144967C CA2144967C CA002144967A CA2144967A CA2144967C CA 2144967 C CA2144967 C CA 2144967C CA 002144967 A CA002144967 A CA 002144967A CA 2144967 A CA2144967 A CA 2144967A CA 2144967 C CA2144967 C CA 2144967C
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- cis
- cyclopentane
- beta
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 title claims description 12
- PRLVHZDMICRVJF-UHFFFAOYSA-N cyclopentane;heptanoic acid Chemical compound C1CCCC1.CCCCCCC(O)=O PRLVHZDMICRVJF-UHFFFAOYSA-N 0.000 title abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 title abstract description 11
- 229940124597 therapeutic agent Drugs 0.000 title description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 122
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims abstract description 67
- -1 nitro, amino Chemical group 0.000 claims abstract description 47
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 150000003573 thiols Chemical class 0.000 claims abstract description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 6
- 230000035939 shock Effects 0.000 claims abstract description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 150000002923 oximes Chemical class 0.000 claims abstract description 5
- 208000019693 Lung disease Diseases 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 150000003254 radicals Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 206010030043 Ocular hypertension Diseases 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 4
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- 230000000241 respiratory effect Effects 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
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- 208000021822 hypotensive Diseases 0.000 abstract description 4
- 239000000050 smooth muscle relaxant Substances 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 206010021639 Incontinence Diseases 0.000 abstract description 2
- 208000010643 digestive system disease Diseases 0.000 abstract description 2
- 230000035558 fertility Effects 0.000 abstract description 2
- 208000018685 gastrointestinal system disease Diseases 0.000 abstract description 2
- 230000009885 systemic effect Effects 0.000 abstract description 2
- 125000000101 thioether group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- 150000003180 prostaglandins Chemical class 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 13
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000872 buffer Substances 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 230000004410 intraocular pressure Effects 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
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- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 4
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- 238000003818 flash chromatography Methods 0.000 description 4
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- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 description 3
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- HYHRQSRVNNJKDC-UHFFFAOYSA-N cyclopentane;hept-2-enoic acid Chemical compound C1CCCC1.CCCCC=CC(O)=O HYHRQSRVNNJKDC-UHFFFAOYSA-N 0.000 description 3
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
- C07C247/10—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated and containing rings
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
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- C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/948,056 US5352708A (en) | 1992-09-21 | 1992-09-21 | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US07/948,056 | 1992-09-21 | ||
| PCT/US1993/008472 WO1994006433A1 (en) | 1992-09-21 | 1993-09-09 | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2144967A1 CA2144967A1 (en) | 1994-03-31 |
| CA2144967C true CA2144967C (en) | 2003-11-11 |
Family
ID=25487188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002144967A Expired - Lifetime CA2144967C (en) | 1992-09-21 | 1993-09-09 | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5352708A (de) |
| EP (1) | EP0660716B1 (de) |
| JP (3) | JP3681068B2 (de) |
| AT (1) | ATE209494T1 (de) |
| AU (1) | AU676492B2 (de) |
| CA (1) | CA2144967C (de) |
| DE (2) | DE10299037I2 (de) |
| DK (1) | DK0660716T3 (de) |
| ES (1) | ES2166364T3 (de) |
| LU (1) | LU90957I2 (de) |
| NL (1) | NL300099I2 (de) |
| PT (1) | PT660716E (de) |
| WO (1) | WO1994006433A1 (de) |
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-
1992
- 1992-09-21 US US07/948,056 patent/US5352708A/en not_active Expired - Lifetime
-
1993
- 1993-09-09 DE DE2002199037 patent/DE10299037I2/de active Active
- 1993-09-09 JP JP50815594A patent/JP3681068B2/ja not_active Expired - Lifetime
- 1993-09-09 AU AU48526/93A patent/AU676492B2/en not_active Expired
- 1993-09-09 DE DE69331233.5T patent/DE69331233C5/de not_active Expired - Lifetime
- 1993-09-09 DK DK93921435T patent/DK0660716T3/da active
- 1993-09-09 EP EP93921435A patent/EP0660716B1/de not_active Expired - Lifetime
- 1993-09-09 PT PT93921435T patent/PT660716E/pt unknown
- 1993-09-09 CA CA002144967A patent/CA2144967C/en not_active Expired - Lifetime
- 1993-09-09 WO PCT/US1993/008472 patent/WO1994006433A1/en active IP Right Grant
- 1993-09-09 ES ES93921435T patent/ES2166364T3/es not_active Expired - Lifetime
- 1993-09-09 AT AT93921435T patent/ATE209494T1/de active
-
1995
- 1995-01-11 US US08/371,339 patent/US5607978A/en not_active Expired - Lifetime
-
2002
- 2002-09-04 LU LU90957C patent/LU90957I2/fr unknown
- 2002-09-05 NL NL300099C patent/NL300099I2/nl unknown
-
2004
- 2004-07-08 JP JP2004201577A patent/JP2004346080A/ja not_active Withdrawn
-
2010
- 2010-12-02 JP JP2010269407A patent/JP2011052014A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP3681068B2 (ja) | 2005-08-10 |
| EP0660716B1 (de) | 2001-11-28 |
| US5607978A (en) | 1997-03-04 |
| JP2011052014A (ja) | 2011-03-17 |
| WO1994006433A1 (en) | 1994-03-31 |
| ES2166364T3 (es) | 2002-04-16 |
| AU676492B2 (en) | 1997-03-13 |
| DE69331233C5 (de) | 2014-06-18 |
| DE10299037I1 (de) | 2003-02-20 |
| DE69331233D1 (de) | 2002-01-10 |
| JPH08501310A (ja) | 1996-02-13 |
| JP2004346080A (ja) | 2004-12-09 |
| DE69331233T2 (de) | 2002-06-27 |
| PT660716E (pt) | 2002-05-31 |
| DK0660716T3 (da) | 2002-04-02 |
| AU4852693A (en) | 1994-04-12 |
| DE10299037I2 (de) | 2004-09-23 |
| NL300099I2 (nl) | 2003-03-01 |
| US5352708A (en) | 1994-10-04 |
| CA2144967A1 (en) | 1994-03-31 |
| EP0660716A1 (de) | 1995-07-05 |
| LU90957I2 (fr) | 2003-04-30 |
| NL300099I1 (nl) | 2002-11-01 |
| ATE209494T1 (de) | 2001-12-15 |
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